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Topic: Uses of Finkelstein reaction  (Read 4352 times)

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Offline DanielGeltman

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Uses of Finkelstein reaction
« on: April 15, 2015, 10:49:51 AM »
Hello,

What are the uses of Finkelstein reaction?

Many thanks!

Offline Dan

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Re: Uses of Finkelstein reaction
« Reply #1 on: April 15, 2015, 11:36:16 AM »
There is a vast amount of information in textbooks/google searches/Wikipedia. What have you found so far?
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Offline DanielGeltman

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Re: Uses of Finkelstein reaction
« Reply #2 on: April 15, 2015, 12:20:48 PM »
The funny thing is that although as you say "There is a vast amount of information" I did not find something useful. It says everywhere that this reaction is used a lot, but there are no examples for these uses at all.

Any information you have will be helpful.

Offline sjb

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Re: Uses of Finkelstein reaction
« Reply #3 on: April 15, 2015, 12:34:10 PM »
Hello,

What are the uses of Finkelstein reaction?

Many thanks!

What is the Finkelstein reaction?

Offline DanielGeltman

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Re: Uses of Finkelstein reaction
« Reply #4 on: April 15, 2015, 12:40:03 PM »
Conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone.

Offline orgopete

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Re: Uses of Finkelstein reaction
« Reply #5 on: April 15, 2015, 05:54:46 PM »

What are the uses of Finkelstein reaction?


Uh, to make an iodide? What is the real question?
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Offline Dan

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Re: Uses of Finkelstein reaction
« Reply #6 on: April 16, 2015, 06:00:38 AM »
Conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone.

That's it. It only has one use: Making alkyl halides.

http://www.organic-chemistry.org/namedreactions/finkelstein-reaction.shtm
« Last Edit: April 16, 2015, 06:34:34 AM by Dan »
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Offline Babcock_Hall

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Re: Uses of Finkelstein reaction
« Reply #7 on: April 16, 2015, 09:54:32 AM »
@OP, Why do you think it might be useful to convert an alkyl chloride into an alkyl iodide?  Think about reactivity.  BTW, I have found this reaction to be helpful in my own work.

Offline Enthalpy

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Re: Uses of Finkelstein reaction
« Reply #8 on: April 16, 2015, 11:32:49 AM »
And the difficulty to obtain an iodide versus a bromide, for instance by alkane halogenation.

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For my information:

How slow would a Finkelstein be to change a secondary alkyl bromide in iodide? Is it like: put 1% reactant in 99% solvent, wait for a complete day to obtain something? Or its it possible to give it a huge kick to treat tens of kilograms per hour with a big pot?

Due to the solubility of NaI in acetone, I have a bad feeling. But at least if the Br <-> I swap proceeds ruckzuck and ratzfatz, it must be possible to replenish the NaI on the fly.

Offline Enthalpy

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Re: Uses of Finkelstein reaction
« Reply #9 on: April 26, 2015, 07:09:10 AM »
I have found "few minutes at +50°C" to replace a secondary bromide by an iodide, but this was just to observe a precipitate and distinguish the position and nature of the halide. It doesn't mean that all bromide is converted.

So: how fast is a conversion?

I still haven't found an other answer:
Where does the reaction happen? In the solvent, or at the NaBr surface?

Thank you!

Offline Dan

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Re: Uses of Finkelstein reaction
« Reply #10 on: April 26, 2015, 01:05:26 PM »
So: how fast is a conversion?

That's like asking "how long does it take to bake a cake?"

It depends on the type of cake.
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